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The short answer is that yes of course he can sue for any money owed to him.

It might be worth giving a little more detail about the tenancy. Is it an assured shorthold? Has any fixed period ended? How much is the weekly rent?

Some other things to check are has your friend issued a rent book (a legal requirement for a weekly tenancy) and an address for service of notices (section 48 Landlord and Tenant Act 1987)? Both of these are easily rectified, but if he has not done one or the other then no rent is due until they are sorted out.

Comment

1. L can sue but only for a maximum of six years arrears.
2. Rent Books are needed only if the rent is reserved weekly.
3. L needs to give T an E&W address [s.48 of LTA 1987] in writing.
4. How come L is so clueless, by the way?

It is for the tenant to surrender their lease, and then for the landlord to accept (or not). A s21 notice by itself, and for that matter a tenant leaving as a result of the notice is probably not sufficient to meet the standard required for surrender by operation of law.

This is a bit of an unusual situation and I'm not sure what to do... long story short, my tenant stopped paying their rent in June and has given me several reasons why they couldn't pay. I tried my best to be accommodating, as I thought it's best to do that and try to come to an amicable arrangement...

I've heard that one before.
It's always mistaken.
Any tenant would take care the property they rent, in fact they have to (the property has to be returned in the condition it was given less fair wear and tear otherwise the landlord can claim compensation - regardless of who the tenant is)....

In English law, the principle is, essentially, that the law is what it says, not what was meant.
When you read appeals cases, the amount of time spent looking at definitions and trying to match the precise wording to the precise situation is testament to this.